CAS 485-80-3

5′-[[(3S)-3-Amino-3-carboxypropyl]methylsulfonio]-5′-deoxyadenosine

Description:

5′-[[(3S)-3-Amino-3-carboxypropyl]methylsulfonio]-5′-deoxyadenosine, commonly referred to as S-adenosylhomocysteine (SAH), is a sulfonium compound derived from adenosine. It plays a crucial role in cellular metabolism, particularly in the transfer of methyl groups in various biochemical reactions. The structure features a deoxyadenosine moiety linked to a propylsulfonium group, which contributes to its biological activity. SAH is involved in the regulation of methylation processes, influencing gene expression and protein function. It is also a product of the methylation reactions catalyzed by S-adenosylmethionine (SAM), serving as a key intermediate in the methionine cycle. The compound is soluble in water and exhibits a zwitterionic nature due to the presence of both positive and negative charges. Its biological significance extends to its role as a potential indicator of cellular methylation status and its involvement in various metabolic pathways. Understanding SAH's characteristics is essential for exploring its implications in health and disease, particularly in relation to methylation disorders and cardiovascular health.

Formula: C₁₅H₂₃N₆O₅S

InChI: InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1

InChI key: InChIKey=MEFKEPWMEQBLKI-AIRLBKTGSA-O

SMILES: O[C@H]1[C@H](N2C=3C(N=C2)=C(N)N=CN3)O[C@H](C[S+](CC[C@@H](C(O)=O)N)C)[C@H]1O

Synonyms:

• 5′-[[(3S)-3-Amino-3-carboxypropyl]methylsulfonio]-5′-deoxyadenosine
• Adenosine, 5′-[(3-amino-3-carboxypropyl)methylsulfonio]-5′-deoxy-, (3S)-
• Adenosine, 5′-[(3-amino-3-carboxypropyl)methylsulfonio]-5′-deoxy-, <span class="text-smallcaps">L</span>-
• Adenosine, 5′-[[(3S)-3-amino-3-carboxypropyl]methylsulfonio]-5′-deoxy-
• S-adenosylmethionine
• Adenosine, 5′-[(3-amino-3-carboxypropyl)methylsulfonio]-5′-deoxy-, L-

S-(5'-Adenosyl)-L-methionine Disulfate Salt (Synthetic) (Mixture of Diastereomers)

CAS: 24346-00-7, 485-80-3

Stability Hygroscopic
Applications Methyl donor; cofactor for enzyme-catalyzed methylations, including catechol O-methyltransferase (COMT) and DNA methyltransferases (DNMT). Although present in all cells, it is concentrated in liver where 85% of all methylation reactions occur. It is also involved in regulating liver function, growth, and response to injury.
References Friedel, H., et al.: Drugs, 38, 389 (1989), Lu, S., et al.: Int. J. Biochem. Cell Biol., 32, 391 (2000), Amin, K., et al.: Pharm. Res., 18, 914 (2001),

Formula: C₁₅H₂₆N₆O₁₃S

Purity: >85%

Color and Shape: Neat

Molecular weight: 594.59

Ref: TR-A291530

S-[5'-Adenosyl(15N5)]-L-methionine Sulfate Salt (Mixture of Diastereomers)

Controlled Product

CAS: 485-80-3

Formula: C₁₅H₂₃NN₅O₅S

Color and Shape: Neat

Molecular weight: 501.47

Ref: TR-A146655